diff --git a/pw_env_setup/py/pw_env_setup/cipd_setup/wrapper.py b/pw_env_setup/py/pw_env_setup/cipd_setup/wrapper.py
index 3e9b611..787347a 100755
--- a/pw_env_setup/py/pw_env_setup/cipd_setup/wrapper.py
+++ b/pw_env_setup/py/pw_env_setup/cipd_setup/wrapper.py
@@ -185,12 +185,21 @@
             content = res.read()
         except ssl.SSLError:
             print(
-                'Python SSL error--if using system Python try\n'
-                '    sudo pip install certifi.\n'
+                '\n'
+                'Bootstrap: SSL error in Python when downloading CIPD client.\n'
+                'If using system Python try\n'
+                '\n'
+                '    sudo pip install certifi\n'
+                '\n'
                 'If using Homebrew Python try\n'
+                '\n'
                 '    brew install openssl\n'
                 '    brew uninstall python\n'
-                '    brew install python\n',
+                '    brew install python\n'
+                '\n'
+                "Otherwise, check that your machine's Python can use SSL, "
+                'testing with the httplib module on Python 2 or http.client on '
+                'Python 3.',
                 file=sys.stderr)
             raise